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#$Date: 2022-07-23 02:30:02 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276813 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/51/7245162.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245162
loop_
_publ_author_name
'Tan, Sang Loon'
'Lo, Kong Mun'
'Tan, Yee Seng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Structural systematics in the isomorphous binary co-crystal solvates
 comprising 2,2'-dithiodibenzoic acid, 4-halobenzoic acid and
 dimethylformamide (1:1:1), for halide = chloride, bromide and iodide
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00094F
_journal_year                    2022
_chemical_formula_moiety         'C14 H10 O4 S2, C7 H5 Br O2, C3 H7 N O'
_chemical_formula_sum            'C24 H22 Br N O7 S2'
_chemical_formula_weight         580.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-15 deposited with the CCDC.	2022-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                94.3040(10)
_cell_angle_beta                 99.6680(10)
_cell_angle_gamma                97.8600(10)
_cell_formula_units_Z            2
_cell_length_a                   7.46320(10)
_cell_length_b                   7.62430(10)
_cell_length_c                   21.9289(4)
_cell_measurement_reflns_used    20795
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3280
_cell_measurement_theta_min      5.8750
_cell_volume                     1212.36(3)
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2017)'
_computing_molecular_graphics
;
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
;
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            30664
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.577
_diffrn_reflns_theta_min         4.111
_exptl_absorpt_coefficient_mu    4.324
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_description       slab
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5088
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0289P)²+1.3142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0699
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4918
_reflns_number_total             5088
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00094f2.cif
_cod_data_source_block           shelx_CCDC2
_cod_database_code               7245162
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.625
_shelx_estimated_absorpt_t_max   0.772
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.95582(3) 1.25511(3) 0.33047(2) 0.02267(7) Uani 1 1 d . . . . .
O1 O 0.7573(2) 0.56226(17) 0.50290(6) 0.0220(3) Uani 1 1 d . . . . .
O2 O 0.63546(19) 0.77647(17) 0.54947(6) 0.0208(3) Uani 1 1 d D . . . .
H2O H 0.606(4) 0.698(3) 0.5722(10) 0.031 Uiso 1 1 d D U . . .
C1 C 0.7224(2) 0.7147(2) 0.50688(8) 0.0150(3) Uani 1 1 d . . . . .
C2 C 0.7748(2) 0.8459(2) 0.46388(8) 0.0142(3) Uani 1 1 d . . . . .
C3 C 0.8567(2) 0.7911(2) 0.41436(8) 0.0171(3) Uani 1 1 d . . . . .
H3 H 0.876267 0.671010 0.408220 0.020 Uiso 1 1 calc R U . . .
C4 C 0.9094(2) 0.9123(2) 0.37415(8) 0.0179(3) Uani 1 1 d . . . . .
H4 H 0.964341 0.876162 0.340154 0.021 Uiso 1 1 calc R U . . .
C5 C 0.8805(2) 1.0876(2) 0.38447(8) 0.0167(3) Uani 1 1 d . . . . .
C6 C 0.7988(2) 1.1446(2) 0.43307(8) 0.0179(3) Uani 1 1 d . . . . .
H6 H 0.779845 1.264898 0.439102 0.022 Uiso 1 1 calc R U . . .
C7 C 0.7452(2) 1.0220(2) 0.47280(8) 0.0167(3) Uani 1 1 d . . . . .
H7 H 0.688123 1.058338 0.506234 0.020 Uiso 1 1 calc R U . . .
S1 S 0.47514(6) 0.54166(5) 0.74293(2) 0.01594(9) Uani 1 1 d . . . . .
S2 S 0.51396(5) 0.58202(5) 0.83790(2) 0.01396(9) Uani 1 1 d . . . . .
O3 O 0.55318(18) 0.53539(16) 0.62535(6) 0.0178(3) Uani 1 1 d . . . . .
O4 O 0.7092(2) 0.33807(17) 0.58547(6) 0.0224(3) Uani 1 1 d D . . . .
H4O H 0.720(4) 0.413(3) 0.5596(10) 0.034 Uiso 1 1 d D U . . .
O5 O 0.57822(17) 0.68165(17) 0.95948(6) 0.0192(3) Uani 1 1 d . . . . .
O6 O 0.36640(18) 0.76372(18) 1.01265(6) 0.0214(3) Uani 1 1 d D . . . .
H6O H 0.458(2) 0.812(3) 1.0384(10) 0.032 Uiso 1 1 d D U . . .
C8 C 0.6129(2) 0.3935(2) 0.62648(8) 0.0145(3) Uani 1 1 d . . . . .
C9 C 0.5834(2) 0.2684(2) 0.67367(8) 0.0138(3) Uani 1 1 d . . . . .
C10 C 0.6208(2) 0.0951(2) 0.66343(8) 0.0172(3) Uani 1 1 d . . . . .
H10 H 0.667022 0.061425 0.627195 0.021 Uiso 1 1 calc R U . . .
C11 C 0.5914(3) -0.0282(2) 0.70531(9) 0.0190(4) Uani 1 1 d . . . . .
H11 H 0.617374 -0.145693 0.697912 0.023 Uiso 1 1 calc R U . . .
C12 C 0.5237(2) 0.0214(2) 0.75821(8) 0.0168(3) Uani 1 1 d . . . . .
H12 H 0.502282 -0.063123 0.786881 0.020 Uiso 1 1 calc R U . . .
C13 C 0.4871(2) 0.1936(2) 0.76962(8) 0.0142(3) Uani 1 1 d . . . . .
H13 H 0.441562 0.226093 0.806133 0.017 Uiso 1 1 calc R U . . .
C14 C 0.5167(2) 0.3190(2) 0.72777(8) 0.0129(3) Uani 1 1 d . . . . .
C15 C 0.2904(2) 0.5316(2) 0.85683(8) 0.0137(3) Uani 1 1 d . . . . .
C16 C 0.1425(2) 0.4376(2) 0.81416(9) 0.0176(3) Uani 1 1 d . . . . .
H16 H 0.159771 0.398281 0.773705 0.021 Uiso 1 1 calc R U . . .
C17 C -0.0299(2) 0.4010(2) 0.83041(9) 0.0214(4) Uani 1 1 d . . . . .
H17 H -0.129019 0.334532 0.801254 0.026 Uiso 1 1 calc R U . . .
C18 C -0.0587(2) 0.4606(3) 0.88878(10) 0.0221(4) Uani 1 1 d . . . . .
H18 H -0.176960 0.435870 0.899645 0.026 Uiso 1 1 calc R U . . .
C19 C 0.0870(2) 0.5566(2) 0.93108(9) 0.0186(3) Uani 1 1 d . . . . .
H19 H 0.067001 0.599953 0.970767 0.022 Uiso 1 1 calc R U . . .
C20 C 0.2626(2) 0.5909(2) 0.91645(8) 0.0146(3) Uani 1 1 d . . . . .
C21 C 0.4181(2) 0.6832(2) 0.96455(8) 0.0156(3) Uani 1 1 d . . . . .
O7 O 0.63969(18) 0.91239(18) 1.09652(6) 0.0220(3) Uani 1 1 d . . . . .
N1 N 0.9498(2) 0.99753(19) 1.11346(7) 0.0172(3) Uani 1 1 d . . . . .
C22 C 0.7915(3) 0.9180(2) 1.07983(8) 0.0178(3) Uani 1 1 d . . . . .
H22 H 0.794038 0.861059 1.040001 0.021 Uiso 1 1 calc R U . . .
C23 C 1.1218(3) 0.9987(3) 1.09056(9) 0.0236(4) Uani 1 1 d . . . . .
H23A H 1.208467 0.946174 1.119809 0.035 Uiso 1 1 calc R U . . .
H23B H 1.174050 1.121503 1.086582 0.035 Uiso 1 1 calc R U . . .
H23C H 1.098730 0.929153 1.049835 0.035 Uiso 1 1 calc R U . . .
C24 C 0.9593(3) 1.0842(3) 1.17552(9) 0.0228(4) Uani 1 1 d . . . . .
H24A H 0.834462 1.087662 1.183558 0.034 Uiso 1 1 calc R U . . .
H24B H 1.024947 1.205837 1.178594 0.034 Uiso 1 1 calc R U . . .
H24C H 1.024730 1.017450 1.206244 0.034 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H2O 111.2(18) . . ?
O1 C1 O2 123.18(16) . . ?
O1 C1 C2 122.65(15) . . ?
O2 C1 C2 114.17(15) . . ?
C7 C2 C3 120.12(16) . . ?
C7 C2 C1 120.93(15) . . ?
C3 C2 C1 118.95(15) . . ?
C4 C3 C2 119.91(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 118.88(16) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.18(16) . . ?
C4 C5 Br1 119.15(13) . . ?
C6 C5 Br1 118.67(13) . . ?
C7 C6 C5 118.54(16) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C2 C7 C6 120.37(16) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C14 S1 S2 104.10(6) . . ?
C15 S2 S1 105.27(6) . . ?
C8 O4 H4O 110.1(19) . . ?
C21 O6 H6O 110.3(19) . . ?
O3 C8 O4 122.88(16) . . ?
O3 C8 C9 123.21(15) . . ?
O4 C8 C9 113.91(14) . . ?
C10 C9 C14 119.52(15) . . ?
C10 C9 C8 118.67(15) . . ?
C14 C9 C8 121.80(15) . . ?
C11 C10 C9 120.98(16) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.39(16) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 120.61(16) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.41(16) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 119.08(15) . . ?
C13 C14 S1 120.71(13) . . ?
C9 C14 S1 120.20(13) . . ?
C16 C15 C20 119.23(16) . . ?
C16 C15 S2 121.94(13) . . ?
C20 C15 S2 118.82(13) . . ?
C15 C16 C17 120.44(17) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 120.63(17) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.21(17) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 121.21(17) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C15 C20 C19 119.23(16) . . ?
C15 C20 C21 121.11(15) . . ?
C19 C20 C21 119.62(16) . . ?
O5 C21 O6 123.96(17) . . ?
O5 C21 C20 122.15(16) . . ?
O6 C21 C20 113.89(15) . . ?
C22 N1 C24 121.24(16) . . ?
C22 N1 C23 121.53(15) . . ?
C24 N1 C23 117.22(15) . . ?
O7 C22 N1 124.83(17) . . ?
O7 C22 H22 117.6 . . ?
N1 C22 H22 117.6 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C5 1.8983(18) . ?
O1 C1 1.225(2) . ?
O2 C1 1.318(2) . ?
O2 H2O 0.839(10) . ?
C1 C2 1.484(2) . ?
C2 C7 1.395(2) . ?
C2 C3 1.397(2) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(2) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
S1 C14 1.7841(17) . ?
S1 S2 2.0476(6) . ?
S2 C15 1.7849(17) . ?
O3 C8 1.225(2) . ?
O4 C8 1.322(2) . ?
O4 H4O 0.839(10) . ?
O5 C21 1.220(2) . ?
O6 C21 1.320(2) . ?
O6 H6O 0.833(10) . ?
C8 C9 1.482(2) . ?
C9 C10 1.396(2) . ?
C9 C14 1.409(2) . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(2) . ?
C13 H13 0.9500 . ?
C15 C16 1.394(2) . ?
C15 C20 1.409(2) . ?
C16 C17 1.390(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.396(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.486(2) . ?
O7 C22 1.244(2) . ?
N1 C22 1.323(2) . ?
N1 C24 1.454(2) . ?
N1 C23 1.454(2) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 -175.04(17) . . . . ?
O2 C1 C2 C7 5.0(2) . . . . ?
O1 C1 C2 C3 4.2(3) . . . . ?
O2 C1 C2 C3 -175.77(16) . . . . ?
C7 C2 C3 C4 0.3(3) . . . . ?
C1 C2 C3 C4 -178.97(16) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 Br1 179.01(13) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
Br1 C5 C6 C7 -179.49(13) . . . . ?
C3 C2 C7 C6 -0.8(3) . . . . ?
C1 C2 C7 C6 178.46(16) . . . . ?
C5 C6 C7 C2 0.5(3) . . . . ?
O3 C8 C9 C10 166.13(17) . . . . ?
O4 C8 C9 C10 -13.7(2) . . . . ?
O3 C8 C9 C14 -13.0(3) . . . . ?
O4 C8 C9 C14 167.19(16) . . . . ?
C14 C9 C10 C11 0.7(3) . . . . ?
C8 C9 C10 C11 -178.45(16) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C9 0.3(2) . . . . ?
C12 C13 C14 S1 -178.53(13) . . . . ?
C10 C9 C14 C13 -0.9(2) . . . . ?
C8 C9 C14 C13 178.25(15) . . . . ?
C10 C9 C14 S1 177.99(13) . . . . ?
C8 C9 C14 S1 -2.9(2) . . . . ?
S2 S1 C14 C13 27.33(15) . . . . ?
S2 S1 C14 C9 -151.50(12) . . . . ?
S1 S2 C15 C16 15.93(15) . . . . ?
S1 S2 C15 C20 -163.23(12) . . . . ?
C20 C15 C16 C17 -0.7(2) . . . . ?
S2 C15 C16 C17 -179.85(13) . . . . ?
C15 C16 C17 C18 1.4(3) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C17 C18 C19 C20 -1.4(3) . . . . ?
C16 C15 C20 C19 -1.0(2) . . . . ?
S2 C15 C20 C19 178.16(13) . . . . ?
C16 C15 C20 C21 176.72(15) . . . . ?
S2 C15 C20 C21 -4.1(2) . . . . ?
C18 C19 C20 C15 2.1(3) . . . . ?
C18 C19 C20 C21 -175.68(16) . . . . ?
C15 C20 C21 O5 -14.4(3) . . . . ?
C19 C20 C21 O5 163.29(17) . . . . ?
C15 C20 C21 O6 166.26(15) . . . . ?
C19 C20 C21 O6 -16.0(2) . . . . ?
C24 N1 C22 O7 1.5(3) . . . . ?
C23 N1 C22 O7 -179.83(18) . . . . ?
